Potassium Permanganate Oxidation

Harsh oxidation method used to oxidize primary alcohols to carboxylic acids and secondary alcohols to ketones.

Potassium Permanganate can be used to oxidize primary alcohols to carboxylic acids and secondary alcohols to ketones. This method is harsh and is also suitable for acidic harsh conditions and acid sensitive compound conditions. ¹

Summary

The reaction entry summary. Find the general scheme and full summarized mechanisms here.

General Scheme

This section briefly summarizes what can and cannot undergo reactions.

• 1° Alcohols (Primary) get oxidized to Carboxylic Acids.
• 2° Alcohols (Secondary) get oxidized to Ketones.
• 3° Alcohols (Tertiary) do not get oxidized at all.

Other Conditions

• Potassium Permanganate can be used alongside sulfuric acid to oxidize 1° Alcohols (Primary) to Carboxylic Acids

General Mechanism

This section briefly summarizes steps to find the product and perform the mechanisms.

Quick steps to finding the product for any alcohol

1. Identify the reagents.
2. Assign side chains (non alcohol part).
3. Selectively convert Alcohol to correct product based on alcohol type. Nothing else.
4. Keep the side chains (non alcohol part) the same and piece together the full molecule together again.

Full Primary Alcohol to Carboxylic Acid Mechanism

Full Secondary Alcohol to Ketone Mechanism

Always remember to repeatedly practice your mechanisms and getting your reagents correct. Take advantage of our materials and/or keep practicing on a whiteboard or paper until you get it right every single time.

References

1. Shaabania, A.; Mirzaeia, P.; Naderia, S.; Lee, D. G. Permanganate supported on active manganese dioxide can be used effectively for the oxidation of arenes, alcohols and sulfides under heterogeneous or solvent-free conditions. Tetrahedron 2004, 60, 11415–11420. DOI: 10.1016/j.tet.2004.08.081